Sailing Trips in USA
Top 10 Best USA Sailing Trips
Found 448 Sailing Trips activities in USA. Sort by Popularity. - Page 182 hours - Private Day Sail along Historic St Augustine Bayfront
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More
Private Tour
2 hours - Private Day Sail along Historic St Augustine Bayfront
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USA
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Superb20 reviews5
We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our sta....
Private Tour
Waikiki Private Sunset Sail Romantic and Private
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More
Private Tour
Waikiki Private Sunset Sail Romantic and Private
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USA
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Superb20 reviews5
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....
Private Tour
90 Minute Sailing Tour of Portland
Our tour begins with a cruise across the river to the most expensive floating homes on the Willamette. We then usually head down the historic Holgate channel on Portland's own "Jungle Cruise" to the spectacular city riverfront wh... More
Private Tour
90 Minute Sailing Tour of Portland
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USA
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Very Good5 reviews3.8
Our tour begins with a cruise across the river to the most expensive floating homes on the Willamet....
Private Tour
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)
This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG licensed captain and crew where you'll sail past the Golden Gate Bridge, Alcatraz and Angel Islands and across the San Francisco w... More
Private Tour
2hr. PRIVATE Sailing Experience on San Francisco Bay (6 Guests)
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USA
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Very Good5 reviews3.8
This is a "Private Charter" Sailing Experience on San Francisco Bay for up to 6 guests, with a USCG ....
Private Tour
Private Charter
The captain works with the guest to design a custom outing based on his 30 years of cruising experience in the local area. With knowledge of the local sea conditions and coastal ecology. you build a custom experience. Typically, G... More
Private Tour
Private Charter
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USA
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Superb14 reviews4.8
The captain works with the guest to design a custom outing based on his 30 years of cruising experie....
Private Tour
Chicago Air and Water Show VIP Cruise or Skydeck Experience
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More
Private Tour
Likely to Sell Out Chicago Air and Water Show VIP Cruise or Skydeck Experience
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USA
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Superb2 reviews5
Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chic....
Private Tour
Private Sail Around New York City and The Statue of Liberty
Discover NYC from a completely different perspective on a private sailboat charter. You and your group will view New York City in ways that are breath taking. See the Statue of Liberty up close like you can almost touch it. Sit ba... More
Private Tour
Likely to Sell Out Private Sail Around New York City and The Statue of Liberty
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USA
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Superb7 reviews5
Discover NYC from a completely different perspective on a private sailboat charter. You and your gro....
Private Tour
Sunset Sailing Tour of San Diego Bay up to 6 Guests
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More
Private Tour
Likely to Sell Out Sunset Sailing Tour of San Diego Bay up to 6 Guests
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USA
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Superb1 review5
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....
Private Tour
Likely to Sell Out Half Day Sail Orcas Island
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USA
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Superb15 reviews5
Lessons are private and designed so you can brings friends and family with no extra charge. Up to 6 ....
Private Tour
Sunset Yacht Cruise | Champagne Included | San Diego Bay
What makes this experience truly special is the blend of refined European luxury and a relaxed, intimate atmosphere without the feel of a large group tour. You will be sailing aboard a beautifully crafted French yacht designed for... More
Private Tour
Likely to Sell Out Sunset Yacht Cruise | Champagne Included | San Diego Bay
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USA
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Superb1 review5
What makes this experience truly special is the blend of refined European luxury and a relaxed, inti....
Private Tour
San Diego Private Morning Sail up to 12 guests
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More
Private Tour
Likely to Sell Out San Diego Private Morning Sail up to 12 guests
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USA
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Superb33 reviews5
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....
Private Tour
3 Hour Luxury Private Sailing Catamaran for 7-12 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
Private Tour
Likely to Sell Out 3 Hour Luxury Private Sailing Catamaran for 7-12 People
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USA
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Superb33 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat
When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! You'll sail around Shell Island into the Gulf of Mexico, while you enjoy dol... More
Private Tour
Likely to Sell Out Private Sunset & Dolphin Sightseeing Sail on Daydreams Sailboat
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USA
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Superb2 reviews5
When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you....
Private Tour
Small Group Sunset Sail in San Diego- Public Sail up to 6 guests
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perfect for solo travelers, couples, or friends looking to experience the bay from the water without booking a private charter. Relax ... More
Private Tour
Likely to Sell Out Small Group Sunset Sail in San Diego- Public Sail up to 6 guests
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USA
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Superb73 reviews5
Join Sea Monkey Adventures for a 2-hour sailing tour on San Diego Bay. This small-group sail is perf....
Private Tour
New York Fall Foliage Sail up the Hudson River
Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Schooner America 2.0, both 1800s-style sailboats. Bordering the Hudson River north of Fort Lee, New Jersey, the Palisade Cliffs are am... More
Private Tour
Likely to Sell Out New York Fall Foliage Sail up the Hudson River
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USA
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Exellent11 reviews4.5
Enjoy a 3.5-hour scenic sail up the Hudson River to the Palisades aboard Schooner Adirondack or Scho....
Private Tour
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designe... More
Private Tour
Likely to Sell Out 2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
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USA
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Superb2 reviews5
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....
Private Tour
Private Catamaran: Snorkel, Swim and Dolphin Watching
Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.... More
Private Tour
Likely to Sell Out Private Catamaran: Snorkel, Swim and Dolphin Watching
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USA
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Superb1 review5
Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion....
Private Tour
Private Sailing Experience on Galveston Bay
See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to travel aboard our luxury charter yacht. We offer the perfect blend of comfort and adventure, making it the ... More
Private Tour
Likely to Sell Out Private Sailing Experience on Galveston Bay
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USA
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Superb1 review5
See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and....
Private Tour
Private Whale Watching Sailing Adventure
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More
Private Tour
Likely to Sell Out Private Whale Watching Sailing Adventure
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USA
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Good2 reviews3.5
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....
Private Tour
Sailing Charter
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make an adventure out of it, and sail a living legend out of scenic Sequim Bay! Ingrid Princess is an ocean going, full keel ketch avail... More
Private Tour
Likely to Sell Out Sailing Charter
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USA
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Superb5 reviews5
Experiencing the Olympic Peninsula wouldn’t be complete without a little time on the water. Make a....
Private Tour